2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-3-naphthalen-1-yl-propionamide

Base Information

• Chemical Name: 2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-3-naphthalen-1-yl-propionamide
• CAS No.: 851596-59-3
• Molecular Formula: C₃₄H₃₀N₂O₂
• Molecular Weight: 498.624
• Mol file: 851596-59-3.mol

Synonyms:2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-3-naphthalen-1-yl-propionamide

Chemical Property of 2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-3-naphthalen-1-yl-propionamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-3-naphthalen-1-yl-propionamide

There total 4 articles about 2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-3-naphthalen-1-yl-propionamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.0%

2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-acetamide (599177-26-1) + 2-(bromomethyl)naphthalene (3163-27-7) → 2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-3-naphthalen-1-yl-propionamide (851596-59-3)

Guidance literature:

With potassium hydroxide; N-spiro chiral quaternary ammonium bromide; In toluene; at 0 ℃; for 6h;

DOI:10.1021/ja0459328

Reference yield:

[(benzyl-methoxy-carbamoyl)-methyl]-carbamic acid benzyl ester (851596-56-0) → 2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-3-naphthalen-1-yl-propionamide (851596-59-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: H₂ / Pd/C / methanol / 12 h / 20 °C

2.1: HCl / methanol / 0 - 20 °C

2.2: CH₂Cl₂ / 6 h / 20 °C

3.1: 98 percent / aq. KOH; N-spiro chiral quaternary ammonium bromide / toluene / 6 h / 0 °C

With hydrogenchloride; potassium hydroxide; N-spiro chiral quaternary ammonium bromide; hydrogen; palladium on activated charcoal; In methanol; toluene;

DOI:10.1021/ja0459328

Reference yield:

N-benzyl-N-methoxyamine (20056-98-8) → 2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-3-naphthalen-1-yl-propionamide (851596-59-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-methylmorpholine; ethyl chloroformate / CH₂Cl₂ / 0.25 h / 0 °C

1.2: 79 percent / CH₂Cl₂ / 3.3 h / 0 - 20 °C

2.1: H₂ / Pd/C / methanol / 12 h / 20 °C

3.1: HCl / methanol / 0 - 20 °C

3.2: CH₂Cl₂ / 6 h / 20 °C

4.1: 98 percent / aq. KOH; N-spiro chiral quaternary ammonium bromide / toluene / 6 h / 0 °C

With 4-methyl-morpholine; hydrogenchloride; potassium hydroxide; N-spiro chiral quaternary ammonium bromide; hydrogen; chloroformic acid ethyl ester; palladium on activated charcoal; In methanol; dichloromethane; toluene;

DOI:10.1021/ja0459328

upstream raw materials:

2-(benzhydrylidene-amino)-N-benzyl-N-methoxy-acetamide

2-(bromomethyl)naphthalene

[(benzyl-methoxy-carbamoyl)-methyl]-carbamic acid benzyl ester

N-benzyl-N-methoxyamine

Downstream raw materials:

(2R)-2-diphenylmethyleneamino-1-(1-naphthyl)pentan-3-one

(2R,3R)-2-diphenylmethyleneamino-1-(1-naphthyl)-3-phenylpentan-3-ol

(2R,3S)-2-diphenylmethylamino-1-(1-naphthyl)-3-phenylpentan-3-ol

(1S,2R)-N-Boc-2-amino-3-(1-naphthyl)-1-phenylpropan-1-ol